


The Bet

by Paidendryl



Series: Story Requests [1]
Category: Gravity Falls
Genre: All of Bill's Friends obviously, Anxiety, I change the tags as I go, I don't know, M/M, NERVOUS DIPPER, Slow Burn, but he's also pretty tough when he needs to be, lots I guess?, smut stuff
Language: English
Status: In-Progress
Published: 2016-08-17
Updated: 2016-08-17
Packaged: 2018-08-09 08:30:37
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,249
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7794718
Author URL: https://archiveofourown.org/users/Paidendryl/pseuds/Paidendryl
Summary: <blockquote class="userstuff">
              <p>Story request by Anon on Tumblr</p>
<p> </p>
<p>Bill makes a bet to get into Dipper’s pants. The results? Better than you think.</p>
            </blockquote>





	The Bet

**Author's Note:**

> Request made by Anon on Tumblr: _I really enjoy your writing style, so I just had story request (cause I haven't seen anyone do it so far). Could you write a story where Bill makes a bet with someone to get into Dipper's pants? It's messed up but just Bill bragging about his skills to his friends and showing his progress of getting. Bonus points, if Dipper finds out about the whole bet thing when Bill starts to fall for him or something, and angst. I really love your stuff but don't feel pressured because I'm asking for a lot_

Dipper stared down at the warm, white paper in front of him, the words and numbers clashed together in the form of his newest class that he had just switched to. He sighed, pushing his black framed glasses back before looking over the courses he would be taking for the remaining semester; they were all the same, except for his third block which was Pre-Cal Pre-AP. He had changed it to AP since Pre-AP just wasn’t cutting it for him. Puffing his cheeks and releasing the breath he had built up, he lifted his eyes up and glanced towards the numbers placed on the side of the door he was in front of and then looked back down the ones on his schedule.

Yup, they were exactly the same.

He had been standing outside of his third block classroom, his nerves jumbling and making his stomach twist uncomfortably. His gut begged him to leave, to skip class and chill in the bathroom. But he knew that would’ve been a crappy thing to do. What kind of impression would that leave on his new fellow classmates? How about his teacher?!

He slumped his shoulders and sighed; there he went again with the overthinking. His twin sister Mabel had tried to break him of that horrible habit, but it came with his personality. He supposed he should just go in, he had lunch afterwards and hopefully he could be able to make a friend or two so he wouldn’t have to sit alone, since his other buddies had the second lunch. And he doubted Mabel would be willing to hang with him after this class.

Taking in a deep breath and fixing his posture, Dipper adjusted his backpack’s strap on his shoulder and placed his hands down at his side. The hand holding his schedule gave the paper a small squeeze, making it crinkle slightly. Lifting his hand, he gripped the doorknob before he could change his mind and turned it. He closed his eyes, already imagining the many eyes turning towards him and feeling the anxiety in him rising up. This was it, this was his moment. Would he make a fool of himself or would he actually leave a good enough impression?

His heart thumped loudly against his ribcage, trying to break out and he felt a bead of his sweat slide down the side of his face. His breathing had picked up slightly and he swallowed, trying to bring it back down to a normal level. It wouldn’t do him any good panicking now, especially when he was already beginning to open the door. He snapped his eyes open, watching as the door began to move without his doing so and he was pushed back, nearly stumbling to the floor as he was momentarily caught off guard.

The figure before stared down with slight surprise and annoyance, their green-gold eyes staring into his. Dipper felt his legs go weak and he moved his mouth, trying to form words, but nothing would come out. His mind began whirring to life and he felt his panic rising.

_Oh god, oh god! They’re judging me! I can feel it! This is it-oh lord this is it!_

“Sorry there four eyes,” The figure spoke, their voice calm and indifferent, “I didn’t think anyone was standing here.”

It was followed by a snicker and Dipper felt as though his heart was going to spontaneously combust inside of him. He shifted on his feet, lifting a hand to rub his arm though the thin material of his navy blue jacket. The figure,-or boy, Dipper noticed, was standing a good six feet above him, his straight dirty blonde hair seemed to be tied back in a pony-tail, a very small, short one though, and there was one loose strand that lingered in front of his left eye. He had a lovely golden bronze tan, and his nose was small and curved. He wore tight fitting jeans that showed the curves of his hips, and what appeared to be a long sleeved, gold-yellow button shirt that was untucked and covered the hem of his jeans. Over the shirt was a dark, jet black fishtail parka. As he looked over his outfit, Dipper noticed the long gold chain that hung limply from his neck and had a small, thin golden triangle hanging from it.

He was, in a word, _hot_. The way he carried himself made Dipper feel underdressed and peasant like. And then, it clicked as to who this upstanding, attractive, tall person was.

“Hello?” The boy spoke again, and this time, Dipper could hear a few fellow snickers and looked behind the teen to notice that there was a small crowd surrounding the man. It took him a few moments before it clicked that the bell had rung at some point while he was staring. Students brushed past him from behind and he began sputtering.

“O-oh! S-sorry, I-I didn’t…oh _geez_ ,” He stammered before beginning to back away, his hands held up slightly and a sheepish smile was placed across his growing red face. The boy cocked an eyebrow and gave an amused smile before stepping forward, not paying him another mind as he began walking away with a group of kids who Dipper figured were his friends. His face burned red as he could hear the tell-tale snickers and soft whisperings of the kids passing by and he let out a soft breath.

He had just ran into _the_ Bill Cipher. Popular junior and highest ranking student at Gravity Falls high.

“Way to go, screw up,” he muttered to himself in a chastising manner. He made his way into the now empty classroom and glanced around. It wasn’t much different than his old one. The walls were a brighter white and they were decorated with posters of various encouraging words. Desks were aligned in neat rows facing towards the whiteboard that was riddled with notes and the lesson plans of the day and week. So this was his new AP Pre-Cal class, a class he would be sharing with Bill. His stomach jumped at the thought and he quickly dismissed it. He turned his head to the far left corner and saw his teacher sitting down, her head was bent and she held a red pen his hand. He cleared his throat softly, trying to gain her attention, but it seemed she hadn’t heard him. Swallowing, he walked over towards her, his right hand gripping tightly to the strap of his backpack.

“M-ma’am?” He squeaked, nervousness ringing loudly in his voice. The lady paused, her head snapping up to meet his gaze. Dipper nearly jumped back at the sudden eye contact, but he held his ground and willed himself to calm down, “Hi,” he spoke, “I’m Dipper Pines, your new student.”

The lady raised an eyebrow, her ruby red lips drawn in a thin line, “New, huh?” She said, her voice was slightly scratchy, like she was getting over a small cold, but as far as Dipper could tell, she wasn’t. She leaned back in her black seat, making the chair groan from the sudden shift in weight and she sighed, her hands flipping through the random amounts of papers on her desk. Dipper inwardly cringed at how messy and disorganized she was.

“Yes, I switched to AP since Pre-AP was too easy.”

The lady nodded and pulled out a paper, “Ah, yes. Mr. Pines,” She confirmed, “You missed my class,” She said, handing him several papers. Dipper cringed at the assuming tone in her voice.

“Y-yes, and I’m very sorry about that,” He said, “I uh…was having trouble finding it.”

“See to it that it doesn’t happen again, alright?” The lady said, offering a warm smile. Dipper nodded and returned one himself.

***

The cafeteria was a huge spacious building that was twice the size of the gym at their school. The walls were white, but had a gold and black stripe running across the middle of it. He entered the area, the voices of all the students carrying all over the room. He scoured the room for an empty table and smiled when he finally found one. It was hidden in the back near another exit. There was a round table nearby that was close to a window and Dipper could see the group of students sitting at it. He nearly tripped over his own feet when he noticed that the boy from earlier was sitting at the round table, and immediately he felt his nervousness return.

After his talk with his new teacher, Ms. Peterson, Dipper had no doubt that he would do much better in that class. Not to mention he’d get a better challenge out of it. He got the notion that he was going to get along just fine in that class and would have no trouble excelling in it, despite it being an AP one at that. He forced himself to move again, working his way to the empty table he had set his eyes on and ignored the amount of stares he got from the students he passed by.

Reaching the table without an incident, Dipper sat down unceremoniously and dumped his backpack to the floor. He then leaned forward and rested his forearms along the table’s surface before putting his head down and sighed softly. He listened to the chatter around him and felt himself relaxing a bit. His stomach growled, but he ignored it as usual. He wasn’t feeling hungry and with the way his stomach was twisting up, he felt as though if he even took a bite out of something he would immediately throw it back up.

He tapped his fingers against the hard surface and closed his eyes. Though they snapped back open and he jolted upright immediately when he felt someone land on top of him. His heart started and he turned around to meet the joyful eyes of his sister. Her brown eyes were shining and she held a pure smile of joy.

“Dipper!” She chirped gleefully before plopping down right beside him, “I was worried I wouldn’t be able to find you through all these filled up tables; should’ve known you’d choose the back though,” She chuckled. Dipper steadied himself and snorted, rolling his eyes lazily.

“Relax,” He said, “I wasn’t being anti-social,” he looked around and shrugged, “I just couldn’t find any groups that were looking for new members.”

Mabel scoffed and shook her head. She reached down into her purple, bedazzled messenger bag and pulled out a brown paper bag that held her lunch, “That’s why you’re supposed to just go up and greet them,” Mabel said, swatting his arm playfully. Dipper stuck out his tongue and proceeded to watch her take a bite out of her turkey sandwich, “Speaking of groups,” Mabel said through a mouthful of food, “How’s the supernatural society going?” She said, swallowing her food, “You never gave me the update on it.”

“Eh,” he sighed, “it’s alright. Though it could use a bit more people,” He said.

“Huh…I figured you’d be enjoying it more since you’re all about the _supernatural_ ,” She winked.

Dipper rolled his eyes, knowing just what she was getting at, “Okay, just because I watch the TV show, doesn’t mean I’m into the whole “supernatural” stuff,” Dipper said, squinting his eyes at her. Mabel let out a short, ‘Pfft’ before taking another bite of her food.

“Sure you’re not,” She replied back after swallowing, “I’m your twin, Dipper, I know what you like and dislike. And trust me, you wouldn’t have all those creepy ghost books or weird mystery novels if you didn’t have at least a little love for the weird and abnormal.”

Dipper pursed his lips and looked down at the table, she got him there. “Okay, fine. I _like_ that stuff. You got me there.”

“There ya go! See, was that so hard to admit?” She teased.

Dipper snorted and gave an amused smile before replying, “Very.”

 

***

Bill Cipher sat back in his seat at his group table and grinned as he told his story of last night’s activities. His eyes were meeting each and every gaze of his groups’ as he spoke, “You should’ve seen Dan's expressions last night,” He snickered, “I swear I could’ve just come right then and there just by watching him.”

“So was he as good as Andy?” A short boy asked, his dark grey eyes lit up with curiosity as he nibbled on a barbeque chip. Bill snorted, giving a ‘ _are you kidding_ ’ look to the teen.

“Of course not, Kyrptos,” The taller reprimanded, “But he was easier than him.”

“Really?” A soft piped up. Bill turned to meet his friend Pyronica’s face. Her deep purple irises were staring with surprise at the other. She brushed a pink strand out of her eyes and tucked it behind her ear, “But isn’t he an all good ‘church boy’?” Bill shook his head and stole one of Kryptos’ chips.

“No, you’re thinking of that plump guy with the poofy white hair,” Bill said, biting down on the food he took, “He was a good lay too. But no, Dan was that lanky dude. Y’know Corduroy’s brother?”

Pyronica’s eyes grew big and she gaped at him, “ _Wendy’s brother_?” She said, “But…isn’t he full on straight?”

Bill smirked and leaned back, placing his hands behind his head and giving a smug look, “Well he wasn't last night, "He chuckled, then sighed, "What can I say? Cipher’s charms are irresistible! There is not a person alive in this school who can deny my looks. Too bad most of them aren’t V-teens anymore.”

“What about the Pines?” A gruff voice said.

“The Pines?” Bill said, turning to face the new voice.

The teen named Eight-ball was a tall, skinny student. He wasn’t as tall as Bill, but he was close. He had dark brown hair that was brushed back and light brown eyes. He pointed a thumb over his shoulder and resumed eating the sloppy lunch food served. Bill raised his eyes to peer over at a mostly empty table across from them. He could see two teenagers sitting there, all smiles and laughter. He looked over the first one, taking in the dark, brow curls that riveted down her head and ended down past her shoulders. She had a small, roundish face and a cute nose. When she smiled, Bill could see the braces lined along her teeth. And as far as he could tell, she wore a loose fitting purple tee-shirt. Then his eyes moved towards the boy beside her and recognition fluttered in his eyes.

“Hey, that’s the guy who was standing in front of the door during third,” He said. The boy had short, curly brown hair that flared out at the sides. Like the girl, he had chocolate brown eyes and soft tanned skin. He wore a navy blue jacket and a dull, faded red shirt underneath. He wore also thin, black framed, square glasses that sat neatly on top of his button nose. The teen made eye contact with Bill and seemed to stare at him for a few seconds, his whole being freezing up. Bill stared back, not feeling the awkwardness that the other was feeling. It wasn’t until the girl beside the other snapped her fingers that he looked away and Bill couldn’t help but grin in satisfaction at winning the staring contest that hadn’t existed outside of his mind.

“Not bad. Kind of looks like an airhead though,” Bill mused, once he had finished examining the students, “The girl beside him, that his sister?”

“Yup,” Kryptos said, “Supposedly their twins.”

“Twins, huh?” A boy nicknamed Teeth grinned, “Think they’ll go for a threesome?”

“No way,” Pyronica said as she looked them over, “They’re _way_ too pure for that stuff. Besides, crazy, glitter Pines is dating that guy on the swim team currently, and I don’t think four eyes there would even know what that is, much less commit incest with his own _twin_.”

They all laughed for a moment before Bill got a sly glint in his eye, “Eh, I bet I could make ol’ four eyes turn rogue in a jiffy,” he grinned.

Teeth gave a smirk, “Oh ho, is that so boss?” He teased, “I hear that guys like that are usually the hardest to get into.”

“Yeah!” Eight-ball chortled, “From what I hear, the kid rejected practically everyone that has asked him out. He may seem wimpy, but apparently he’s got a tough side under that soft shell.”

“Where on earth did you hear that?” Pyronica asked. Eight-ball shrugged.

“I like to listen in on the teachers in the teacher’s lounge,” He said, wiping his mouth with the back of his hand, “They like to gossip about all the students.”

“Creepy…but useful,” Bill said, “Guess he’s a forbidden fruit then, huh? Ripe for the picking or whatever.”

“Oh no,” Teeth said, “Are you thinking you have a chance with him? A teen with that kind of reputation is definitely a no-go zone. You’ve got a strong reputation for getting to do everyone at this school, but I don’t think that kind of charm is going to work for a kid like that.”

“Are you doubting my skill?” Bill asked, “I just did Mr. Purely Straight Dan last night! I could get anyone I want and that Pines boy is no exception!”

“Is that a challenge I smell?” Teeth said slyly. Bill grinned like a Cheshire cat.

“Always!” The teen replied, leaning forward, “I bet you that I could get V-boy Pines there to have sex with me just like that!” He said, snapping his fingers.

“Careful Bill, we get you’ve got powerful sex charms, but you’re not _that_ good. Pines probably knows about all your sexual relationships just like everyone else and there’s no way he’d consent with you.”

“You forget who you’re talking to Teeth, I could have that Pines kid begging on his knees before you know it.”

“Fine then,” Teeth said, “I bet you fifty bucks that in two weeks, you’ll be no closer to sexing it up with Dipper than you are with world domination.”

Bill laughed and got a mischievous look in his eyes, “Alright, deal. If I win, you gotta dress in drag and do the ‘ _All the Single Ladies_ ’ dance in front of a camera and post it up for the whole entire school to see.”

“Fair enough, and if _I_ win-which I will,” Teeth said smugly, “You got to get a tattoo.”

Bill snickered, “That’s it? I could do it without a bet, Teeth.”

“Hold on, you didn’t let me finish,” Teeth said, “That tattoo has to be one of those silly child stars with a stupid face and the words; ‘ _I’m an all-star_ ’ around it.”

Bill pursed his lips and furrowed his brows, he clicked his tongue and sighed. Never one to back down, he stared straight at his friend and nodded, “Alright. In two weeks, Pines’ V-card will be officially mine. If not, which would be ridiculous by the by, then I will get that embarrassing tattoo. But if I win…”

“So we have a deal?” Teeth asked.

The others at the table stared with wide eyes as they watched Bill contemplate himself for a moment. Then, they watched as his mouth upturned into a wicked grin and he took Teeth’s hand in his own and shook it.

“Deal.”

**Author's Note:**

> Woof, buckle up kids. We're in for a treat! And Anon, I hope this turns out better than what you asked for!
> 
> Apologies for any grammar errors!
> 
>  
> 
> Please leave a comment or a critique (if ya want!)
> 
> Got story prompts or requests? Wanna see art made by me? Wanna bug me just because or ask questions? Go visit me on tumblr--> @paidenzilla


End file.
